N¹,N¹-diethyl-12-phthalimido-1-dodecanamide | 219776-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N¹,N¹-diethyl-12-phthalimido-1-dodecanamide
• 英文别名: 12-(1,3-dioxoisoindol-2-yl)-N,N-diethyldodecanamide
• CAS: 219776-07-5
• 化学式: C₂₄H₃₆N₂O₃
• 分子量: 400.561
• InChiKey: APSSJGIFSYJZPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N¹,N¹-diethyl-12-phthalimido-1-dodecanamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以85%的产率得到12-amino-N¹,N¹-diethyl-1-dodecanamide
  参考文献：
  名称：

  Structure−Activity Relationships for Antiplasmodial Activity among 7-Substituted 4-Aminoquinolines

  摘要：

  Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)(3)NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N,N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7-bromo-AQs with diaminoalkane side chains [-HN(CH2)(2)NEt2, -HN(CH2)(3)NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC(50)s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC(50)s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC(50)s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC(50)s of 17-150 nM) and -resistant P. falciparum (IC(50)s of 90-3000 nM).

  DOI：

  10.1021/jm980146x
• 作为产物：
  描述：

  12-氨基十二酸 在 五氯化磷 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 5.5h， 生成 N¹,N¹-diethyl-12-phthalimido-1-dodecanamide
  参考文献：
  名称：

  摘要：

  The preparation of N-12-(7-chloro-4-quinolinyl)-N-1,N-1-diethyl-1,12-diaminododecane, AQ-40, was accomplished by a five-step process in 80% overall yield from 12-aminododecanoic acid and 4,7-dichloroquinoline. AQ-40 crystallizes as a monohydrate from reagent grade chloroform/ diethyl ether mixtures in the triclinc space group P-1 with a = 8.667(2), b = 8.9425(10), c = 17.217(3) Angstrom, alpha = 99.34(1), beta = 99.89(2), gamma = 91.56(1)degrees V = 1295.0 Angstrom(3) and Z = 2. The 12-(N-1,N-1-diethylamino)dodecyl side chain is in the fully extended conformation and the water molecule forms hydrogen bonds to the two tertiary nitrogen atoms as well as with the secondary amino group. The nitrogen of the secondary amino group bound to the four-position of the quinoline moiety is virtually planar. This together with the rather short C-N distance of 1.347(3) Angstrom to the quinoline moiety suggests involvement of the lone pair on this nitrogen with the pi system of the ring.

  DOI：

  10.1023/a:1022810821793

文献信息

• Structure−Activity Relationships for Antiplasmodial Activity among 7-Substituted 4-Aminoquinolines
  作者：Dibyendu De、Frances M. Krogstad、Larry D. Byers、Donald J. Krogstad

  DOI：10.1021/jm980146x

  日期：1998.12.1

  Aminoquinolines (AQs) with diaminoalkane side chains (-HNRNEt2) shorter or longer than the isopentyl side chain [-HNCHMe(CH2)(3)NEt2] of chloroquine are active against both chloroquine-susceptible and -resistant Plasmodium falciparum. (De, D.; et al. Am. J. Trop. Med. Hyg. 1996, 55, 579-583). In the studies reported here, we examined structure-activity relationships (SARs) among AQs with different N,N-diethyldiaminoalkane side chains and different substituents at the 7-position occupied by Cl in chloroquine. 7-Iodo- and 7-bromo-AQs with diaminoalkane side chains [-HN(CH2)(2)NEt2, -HN(CH2)(3)NEt2, or -HNCHMeCH2NEt2] were as active as the corresponding 7-chloro-AQs against both chloroquine-susceptible and -resistant P. falciparum (IC(50)s of 3-12 nM). In contrast, with one exception, 7-fluoro-AQs and 7-trifluoromethyl-AQs were less active against chloroquine-susceptible P. falciparum (IC(50)s of 15-50 nM) and substantially less active against chloroquine-resistant P. falciparum (IC(50)s of 18-500 nM). Furthermore, most 7-OMe-AQs were inactive against both chloroquine-susceptible (IC(50)s of 17-150 nM) and -resistant P. falciparum (IC(50)s of 90-3000 nM).
• ——
  作者：Dibyendu De、Donald, J. Krogstad、Joel T. Mague

  DOI：10.1023/a:1022810821793

  日期：——

  The preparation of N-12-(7-chloro-4-quinolinyl)-N-1,N-1-diethyl-1,12-diaminododecane, AQ-40, was accomplished by a five-step process in 80% overall yield from 12-aminododecanoic acid and 4,7-dichloroquinoline. AQ-40 crystallizes as a monohydrate from reagent grade chloroform/ diethyl ether mixtures in the triclinc space group P-1 with a = 8.667(2), b = 8.9425(10), c = 17.217(3) Angstrom, alpha = 99.34(1), beta = 99.89(2), gamma = 91.56(1)degrees V = 1295.0 Angstrom(3) and Z = 2. The 12-(N-1,N-1-diethylamino)dodecyl side chain is in the fully extended conformation and the water molecule forms hydrogen bonds to the two tertiary nitrogen atoms as well as with the secondary amino group. The nitrogen of the secondary amino group bound to the four-position of the quinoline moiety is virtually planar. This together with the rather short C-N distance of 1.347(3) Angstrom to the quinoline moiety suggests involvement of the lone pair on this nitrogen with the pi system of the ring.